Trifluoroacetic acid → N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(6-chloro-5-(methylsulfonyl)pyridin-3-yl)acetamide

HRID 592222ノート

反応式

HRID 592222 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([O:11]C(C)(C)C)=O)=[CH:4][C:3]=1[S:16]([CH3:19])(=[O:18])=[O:17].C(O)(C(F)(F)F)=O.[NH2:27][C:28]1[N:33]=[CH:32][C:31]([N:34]2[CH2:39][CH2:38][N:37]([C:40](=[O:42])[CH3:41])[CH2:36][CH2:35]2)=[CH:30][CH:29]=1.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>C(Cl)Cl>[C:40]([N:37]1[CH2:36][CH2:35][N:34]([C:31]2[CH:30]=[CH:29][C:28]([NH:27][C:9](=[O:11])[CH2:8][C:5]3[CH:6]=[N:7][C:2]([Cl:1])=[C:3]([S:16]([CH3:19])(=[O:17])=[O:18])[CH:4]=3)=[N:33][CH:32]=2)[CH2:39][CH2:38]1)(=[O:42])[CH3:41]

参加物

7

反応物 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 284116891-(4-(6-Aminopyridin-3-YL)piperazin-1-YL)ethan-1-oneHCID 58447953Tert-butyl 2-(6-chloro-5-(methylsulfonyl)pyridin-3-yl)acetate

生成物 1

HCID 86657957N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(6-chloro-5-(methylsulfonyl)pyridin-3-yl)acetamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of tert-butyl 2-(6-chloro-5-(methylsulfonyl)pyridin-3-yl)acetate 197-5 (40 mg, 0.13 mmol) and TFA (0.5 mL) in DCM (3 mL) was stirred at room temperature for 2 hours. The solvents were evaporated to dryness under high vacuum. The crude product, 2-(6-chloro-5-(methylsulfonyl)pyridin-3-yl)acetic acid 197-6, was dissolved in DMF (2 mL). 1-(4-(6-aminopyridin-3-yl)piperazin-1-yl)ethanone (35 mg, 0.16 mmol) and DIEA (114 uL, 0.65 mmol) were added to the solution before O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (75 mg, 0.20 mmol). The mixture was stirred at room temperature overnight. The solvent was removed by rotary evaporation. The residue was purified by silica gel flash chromatography and eluted with 5% MeOH in CH2Cl2 to give N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(6-chloro-5-(methylsulfonyl)pyridin-3-yl)acetamide 197-7. MS m/z 452.1 (M+1).

後処理

  1. customThe solvents were evaporated to dryness under high vacuum
  2. dissolutionThe crude product, 2-(6-chloro-5-(methylsulfonyl)pyridin-3-yl)acetic acid 197-6, was dissolved in DMF (2 mL)
  3. stirringThe mixture was stirred at room temperature overnight
  4. customThe solvent was removed by rotary evaporation
  5. customThe residue was purified by silica gel flash chromatography
  6. washeluted with 5% MeOH in CH2Cl2

出典と根拠

ORDレコード
ord-14e65248eb3b412c8fe4209e7f2a2c28
出典データセット
uspto-grants-2016_01
特許番号
US09238646B2

反応ノート

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